lipstick stains on plain white cards
by Fancy Piece of Work
Summary: She went from kissing boys with girlfriends in the back rooms at school to kissing men with wives in the back of their limos. AU Jenny based. Mentions of D/S and C/B


She started out her years of infamy as one of the many girls wishing to be talked about by Gossip Girl.

She'd subscribed in her last year of middle school and checked her phone religiously every day for two years, hoping the blogger had mentioned her once, just once, even in passing as one of the friends of the popular girls (though God knows she hadn't talked to the girls drenched in pearls worth half her house and enough Chanel No. 5 to kill a small animal even _once_ in her life).

The first time she was mentioned it wasn't in passing at all, but was instead complete with a picture of her with her hands full of another girl's boyfriend and a shiny new nickname. It didn't matter that technically the boy wasn't a real boyfriend, because it was _Serena_ _Van Der Woodsen's_ latest not-boyfriend, and everybody knew Serena's not-boyfriends were _not available_.

Her brother told her dad who told her mum who blamed her dad who blamed society, but she didn't care because the day Gossip Girl first called her Little J was the day she stopped checking her damn phone religiously and started making her way through the polo and lacrosse teams and speaking to the girls in Chanel like they were best friends because suddenly everybody knew her and wanted her and she was now known as the girl who stole from The Upper East Side's It Girl and got away with it (she was even known vaguely as the new Serena in some circles).

She didn't mind so much that the only reason people knew her name was because she was so much like another girl, she'd spent her life being Lonely Boy's little sister and this was a step up really.

* * *

><p>When she was over the thrill of stealing the All-American boys from their All-American girlfriends, she started visiting clubs she was too young for but pretty enough to get into anyway and drinking fancy drinks that made her head fuzzy and her laughter louder.<p>

Business men in expensive suits with matching silk ties would run their hands up along her legs, trailing across her milk skin for miles and leaving a certain scent of royalty it seemed only she could smell. A smell she fell in love with and a smell she'd spend the rest of her life covered in.

She went from kissing boys with girlfriends in the back rooms at school to kissing men with wives in the back of their limos. Gossip Girl changed her nickname from Little J to _Lady J_ and she got her own page on the famous website, right next to Blair Waldorf (who tended to raise her nose at Jenny in public but was caught on camera looking infuriated at the way Lady J was dressed, "How that girl manages to wear Lagerfeld like it belongs on her, I'll never know.") and Georgina Sparks (who nobody really cared about anymore considering she was gone and Jenny was here, but the two names were mentioned together so often Gossip Girl decided to keep Georgina's page up and running if only to be able to compare the two daily).

* * *

><p>She made her very first business card in art class one day, a blank white card with an imprint of her initials she kissed hard, leaving a perfect red outline, and it was a man her father's age she gave it to. Gossip Girl managed to get a picture of Jenny giving it away and called it her V card so she figured she might as well back the silly card up with a visit to the bathroom to give away the only thing she hadn't yet.<p>

She lost her virginity and cemented her notoriety the night she had sex with a man in a pretty suit with a pretty tie he used to tie up her hands behind her back in the bathroom of a loud club. She also gained $3000 in cash because maybe he felt bad for having sex with a fifteen year old- or maybe he just wanted her not to tell on him or something, but it was fine. She didn't care because she needed new shoes and a new bag and a new phone so she kissed him hard and promised not to tell a soul.

Gossip Girl could never confirm a thing (much to her annoyance) but everybody pretty much knew Jenny Humphrey gave her V card to a man whose name she didn't know and for a pretty sum of cash too. Her brother didn't tell her father who didn't tell her mother because they barely even spoke anymore and Dan pretty much only ever spoke to _her_ to tell her to grow up. She moved out when she met a model named Agnes who was like-minded and who had a few friends who could give her the numbers of some people who could give her money for something so meaningless like _sex_.

She never bothers to think that the only reason she even had sex in the first place was because she didnt want Gossip Girl to be wrong about her.

* * *

><p>She never managed to finish school- which included Chuck Bass wrapping an arm around her shoulder every morning and whispering dirty things in her ear and classes filled with Blair Waldorf's ex-minions trying to become best friends with her if only to get names of 'business associates' and whatever else she could spill. Not that she ever did though- spill that is. Her trysts were her secrets and the more people who realised this, the more people who found her number.<p>

Blair made her Queen when she left for Yale (if only to spite everybody who turned on her when Chuck Bass was found out to be her new boyfriend or maybe it was because Jenny was the only person who wished Blair and Chuck luck?) and Queen Jenny's reign lasted long enough for the girls wearing Chanel and pearls to start wearing fishnets and leather jackets before she made some nobody Queen and gave up on Constance and school in general because it's not like she could write 'Hooker' on any college applications, was it?

A few years later and she was a few million dollars richer, living in a beautiful apartment and still friends with that skinny model Agnes.

Agnes had managed to convince her to give modelling a go a few years back and it turned out she pretty good at it. Sitting and looking pretty was her calling it seemed- right after sex with men three times her age. She hadn't spoken to her parents in a while and Dan (who was getting ready to marry Serena) would only call every few weeks, usually at very unlucky times, to try and convince her to leave her scandalous life behind and come back to the 'sanity' of the Upper East Side, but she always refused, laughingly saying her life was fine the way it was, usually while she was getting ready to go out or being kissed by one of her business associates or drinking wine with Agnes.

She didn't mind it like Dan thought she should. It was her life, with both the rush and the security that came with it. Dan couldnt see that a lot had changed since she was fourteen and scrolling down the pages of Gossip Girl searching for her name. Now her name was in magazines and on billboards and in the wallets of men in pretty suits with matching ties who called her by names not her own.


End file.
